The lovefest between New England and Kenny Chesney goes way back to 2005. Maybe it started before that, when he was playing smaller venues like the Worcester Centrum or Boston's Symphony Hall, and the friends who believed in him even then.

I was fortunate enough to meet Kenny before he was a superstar, and we've stayed friends all these years.

Ginny Rogers
Ginny Rogers

He's always so easy to talk to, and I had the chance again to chat with him back in 2022. His voice lit up when we talked about the Red Sox, New England, Gillette Stadium, and his home in St. John.

I asked him about the rumors he was purchasing a house in Gloucester, MA, where he filmed the video for "Knowing You". He did have dinner at Mile Marker One at the Cape Ann Marina following the filming of the video. Chesney says, " I like the Gloucester area. I like fishing and being out on the water."  And we talked about the rumor that he has a home in Maine.

He said anything is possible down the road, but right now, no, he has no house in either of those locations.  "I love the coast of Maine and have a lot of friends in New England, so I just stay with them. I'm pretty basic. I usually want to stay in the summer or fall, but I'm just too busy."  He went on to say "to be on the coast of Maine is just so absolutely beautiful.  I've been out on boats with friends and I love it."

Knowing You video

The two shows at Gillette Stadium always end his tour.  It's been that way for years, saving the best for last.  Kenny says, "It's a double-edged sword, to play there, because we are so excited to be there, but it's like the last day of school in a way, and we're excited to be out of school and be off tour, but we don't want to let it go either."

He goes on to say, "The crowd in Foxborough is such a groundswell of emotion and energy.  It's so amazing, and it's always been a great way for us to end the tour."

His birthday was in late March, so I ask him if he did anything special to celebrate his latest trip around the sun.  He said he was on a strict diet with the tour almost here, and he did not have a beer, but did see someone special he doesn't get to see that often. He told me, "My mom is still very healthy and we don't get to spend a lot of time together, so for the first time in several years, she came down and we just hung out. We didn't do much of anything, but it was good to spend time together and that was a good birthday gift for me."

In September of 2017, Hurricane Irma, followed by Hurricane Maria, devastated the islands that Kenny calls home.  His hilltop home on St. John was leveled, but he vowed to help the people rebuild before he did.  It's now almost four years later, and he will finally have his island home ready sometime this summer.  He took care of everyone else first by starting the "Love for Love City Fund" to help with basics the island folks needed, like food and water, clothing, and books.  The foundation went on to lift the island up to full beauty after many years of perseverance and rebuilding.

He's a philanthropist who helps people in need.  Kenny is a man of character.

Back in 2013, after the Boston Marathon Bombing, Kenny was upset that something like this could happen in his beloved Boston, a city that has supported him year after year on every level.  He was quoted in as saying, "This is a very passionate town. They're passionate about sports. They're passionate about life.  They're passionate about music and food.  And they work really hard.  And those are all the things I grew up on."

Chesney was upset and knew he had to do something for the survivors.

Kenny actually called me and we talked about what he wanted to do.  He wanted to make a difference in the lives of those who particularly lost limbs or were badly injured.  He took a tour of Boston Medical Center and decided to start the "Spread The Love Fund".

Proceeds from that song went to the fund to help finance the current and future care for amputee victims of the bombing.  It's the music that brings people together in the most unusual ways.  Kenny never would have met those survivors who needed prosthetics without the music giving them strength.

Another reason he loves New England is the Boston Red Sox.  He says, "I love going to Fenway, I love it. I've always been a Red Sox fan ever since I was a kid. In Little League I always wanted to be on the Boston Red Sox team, because I loved the Red Sox. I brought my dad to Fenway one year and it was really great for us to do that together."  You will often see him wearing a Red Sox shirt or ball cap, and Patriots gear, too.

Now let's take a look at some of the iconic photos of Kenny Chesney's love for New England.

Kenny Chesney Clears Up Rumors He Has a House in Maine, Talks Love for New England

Kenny Chesney's Love for New England in Photos.

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